# US 10,864,167 B2 · Encapsulation

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- Number: US 10,864,167 B2
- Document ID: US10864167B2
- Status: Granted
- Kind: B2
- Application number: 15/960,654
- Filed: 2018-04-24
- Published: 2018-08-23
- Granted: 2020-12-15
- Earliest claimed: 2015-10-27
- Assignees: The Procter & Gamble Company
- Applicants: The Procter & Gamble Company
- Inventors: Hanwei Zhang; Todd Arlin Schwantes; Katie Ann Hobart; Diane Jean Williamson
- Web page: https://patentgrep.com/patent/US10864167B2

## CPC

- A61K 9/5031: {obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyethylene glycol, poly(lactide-co-glycolide)}
- A01N 25/28: Microcapsules {or nanocapsules}
- A61K 8/11: Encapsulated compositions
- A61K 8/8152: {Homopolymers or copolymers of esters, e.g. (meth)acrylic acid esters; Compositions of derivatives of such polymers}
- A61K 8/87: Polyurethanes
- A61K 8/88: Polyamides
- A61K 9/50: Microcapsules {having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals (A61K9/2081 takes precedence; particles with a single coating comprising drug A61K9/167)}
- A61K 9/5026: {obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone, poly(meth)acrylates}
- A61K 9/5089: {Processes}
- A61L 15/225: {Mixtures of macromolecular compounds}
- A61L 15/46: Deodorants or malodour counteractants, e.g. to inhibit the formation of ammonia or bacteria
- A61L 15/60: Liquid-swellable gel-forming materials, e.g. super-absorbents
- A61Q 5/02: Preparations for cleaning the hair
- A61Q 13/00: Formulations or additives for perfume preparations (essential oils or perfumes per se C11B9/00)
- A61Q 15/00: Anti-perspirants or body deodorants (deodorisation of air A61L9/00)
- A61Q 17/04: Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
- A61Q 19/10: Washing or bathing preparations
- B01J 13/14: Polymerisation; cross-linking
- B01J 13/16: Interfacial polymerisation
- B01J 13/18: In situ polymerisation with all reactants being present in the same phase
- C09B 67/0097: {Dye preparations of special physical nature; Tablets, films, extrusion, microcapsules, sheets, pads, bags with dyes}
- C10M 171/06: Particles of special shape or size
- C11D 3/505: {encapsulated or adsorbed on a carrier, e.g. zeolite or clay}
- C11D 17/0039: {Coated compositions or coated components in the compositions, (micro)capsules}
- F28D 20/023: {the latent heat storage material being enclosed in granular particles or dispersed in a porous, fibrous or cellular structure}
- A61K 2800/412: Microsized, i.e. having sizes between 0.1 and 100 microns
- C10N 2020/055: {Particles related characteristics}
- C10N 2050/12: {Micro capsules}
- Y02E 60/14: Thermal energy storage
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A01N: PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF (preservation of food or foodstuff A23); BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES (preparations for medical, dental or toiletry purposes which kill or prevent the growth or proliferation of unwanted organisms A61K); PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A61L: METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES (preservation of bodies or disinfecting characterised by the agents employed A01N; preserving, e.g. sterilising, food or foodstuffs A23; preparations for medical, dental or toiletry purposes A61K)
- A61Q: SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- C09B: ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES {, e.g. PIGMENTS}; MORDANTS; LAKES (fermentation or enzyme using processes to synthesise a desired chemical compound C12P)
- C10M: LUBRICATING COMPOSITIONS (well drilling compositions C09K8/02); USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION (mould release, i.e. separating, agents for metals B22C3/00, for plastics or substances in a plastic state, in general B29C33/56, for glass C03B40/02; textile lubricating compositions D06M11/00, D06M13/00, D06M15/00; immersion oils for microscopy G02B21/33)
- C11D: DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- F28D: HEAT-EXCHANGE APPARATUS, NOT PROVIDED FOR IN ANOTHER SUBCLASS, IN WHICH THE HEAT-EXCHANGE MEDIA DO NOT COME INTO DIRECT CONTACT (fluid heaters having heat generating means and heat transferring means F24H; furnaces F27; details of heat-exchange apparatus of general)
- C10N: INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION

## Abstract

An improved process of making a benefit agent delivery particle and consumer products incorporating such particles are disclosed. The process comprises the steps of providing a first composition of water phase 1, water phase 2 and water phase 3. Water phase 1 comprises water and an initiator; water phase 2 comprises water, a water-soluble or dispersible amine(meth)acrylate or hydroxyl(meth)acrylate and a multifunctional (meth)acrylate. Water phase 3 comprises water, and carboxyalkyl(meth)acrylate and a base or quaternary ammonium acrylate. The first two water phases are combined to prereact the hydroxy- or amine(meth)acrylate and the multifunctional (meth)acrylate to form a multifunctional hydroxyl-amine(meth)acrylate pre-polymer. The pre-polymer is combined with water phase 3; then an emulsion is formed by emulsifying under high shear agitation a second composition into said first composition; said second composition comprising an oil phase comprising an isocyanate and a benefit agent core material thereby forming a wall surrounding the benefit agent core material.

## Claims

### Claim 1

A consumer product comprising the combination of a consumer product ingredient and microcapsules, the microcapsules having a shell with surface charge functional groups, the microcapsules made by a process comprising:
dispersing in one or more water phases an initiator, and a cross-linking functional monomer having one or more —OH, —NH2, or —NH− groups, and a charge functional monomer having one or more anionic or cationic groups which are selected from carboxy, sulfonic acid, quaternary ammonium groups, or other charged groups;
prereacting the cross-linking functional monomer and the charge-functional monomer in the one or more water phases and combining with a water dispersible multifunctional (meth)acrylate monomer;
further prereacting the cross-linking functional monomers and the charge-functional monomers, forming prereacted monomers;
forming an emulsion by emulsifying into the water phase or phases, using high shear agitation, an oil phase comprising an isocyanate and a benefit agent core material;
optionally adding in addition, an amine cross-linker;
further reacting the combined emulsion of prereacted monomers, water dispersible multifunctional (meth)acrylate monomer, and emulsified oil phase by heating for a time and temperature, or actinic irradiation for a time, sufficient to form a microcapsule shell surrounding the benefit agent core material,
wherein the shell comprises a reaction product of the isocyanate, the prereacted monomers, and the water dispersible multifunctional (meth)acrylate monomer.

### Claim 2 (depends on 1)

The consumer product according to claim 1 wherein the cross-linking functional monomer is an amine.

### Claim 3 (depends on 2)

The consumer product according to claim 2 wherein the amine is an alkylaminoalkyl(meth)acrylate.

### Claim 4 (depends on 1)

The consumer product according to claim 1 wherein the cross-linking functional monomer is hydroxyl functional.

### Claim 5 (depends on 4)

The consumer product according to claim 4 wherein the cross-linking functional monomer is a hydroxyl(meth)acrylate.

### Claim 6

A consumer product comprising the combination of a consumer product ingredient and microcapsules comprising an oil soluble or dispersible benefit agent core material and a shell surrounding the benefit agent core material, the shell comprising a polyurea formed from a first component of an isocyanate and a second component of an amine, the amine comprising the reaction product of an alkylaminoalkyl(meth)acrylate and a multifunctional (meth)acrylate, together with a carboxyalkyl(meth)acrylate or quaternary ammonium acrylate.

### Claim 7 (depends on 6)

The consumer product according to claim 6 wherein the amine is tertiary-butylaminoethylmethacrylate.

### Claim 8 (depends on 6)

A consumer product according to claim 6 wherein the shell of the microcapsules comprises a reaction product of an isocyanate; and a multifunctional amine (meth)acrylate.

### Claim 9 (depends on 6)

The consumer product according to claim 6 wherein the isocyanate is selected from isophorone diisocyanate, 4,4′-methylene diphenyl diisocyanate, 2,2′-methylene diphenyl diisocyanate, and 2,4′-methylene diphenyl diisocyanate.

### Claim 10 (depends on 6)

The consumer product according to claim 6 wherein the alkylaminoalkyl (meth)acrylate is selected wherein each alkyl moiety is independently from C1 to C8.

### Claim 11 (depends on 6)

The consumer product according to claim 6 wherein the alkylamino (meth)acrylate is selected from tertiary-butylaminoethyl methacrylate, tertiary-butylaminopropyl methacrylate, n-butylaminoethyl methacrylate, diethylaminoethyl methacrylate, dimethylaminoethyl methacrylate, diisopropyaminoethyl methacrylate, dibutylaminoethyl methacrylate, dipropylaminoethyl methacrylate, tertiary pentylaminoethyl methacrylate, tertiary hexylaminoethyl methacrylate, tertiary-butylaminopropyl methacrylate, diethylaminopropyl methacrylate, and dimethylaminopropyl methacrylate.

### Claim 12 (depends on 6)

The consumer product according to claim 6 wherein the microcapsule has a zeta potential, measured at a pH of 7, of from +70 to −70.

### Claim 13 (depends on 6)

The consumer product according to claim 6 wherein the benefit agent core material of the microcapsule is selected from one or more of a fragrance, perfume, phase change material, biological active, antimicrobial, self-healing composition, lubricant or cooling agent.

### Claim 14

A consumer product comprising the combination of a consumer product ingredient and microcapsules comprising an oil soluble or dispersible benefit agent core material and a shell surrounding the benefit agent core material, the shell comprising a reaction product of an isocyanate; and a multifunctional amine (meth)acrylate, together with a carboxyalkyl(meth)acrylate, wherein the multifunctional amine(meth)acrylate is selected to be polar.